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Volumn 6, Issue 8, 2005, Pages 1381-1390

An inverse substrate orientation for the regioselective acylation of 3′,5′-diaminonucleosides catalyzed by Candida antarctica lipase B?

Author keywords

Aminolysis; Biotransformations; Enzyme catalysis; Molecular modeling; Nucleosides

Indexed keywords

3',5' DIAMINO 3',5' DIDEOXYTHYMIDINE; 3',5' DIAMINONUCLEOSIDE; ALCOHOL; AMIDE; AMINE; AMINONUCLEOSIDE; AMMONIA; BUTYRIC ACID; CARBONYL DERIVATIVE; ESTER; FUNGAL ENZYME; HISTIDINE; LIPASE B; METHOXYACETIC ACID; OXIME; PHOSPHONIC ACID DERIVATIVE; PHOSPHONOAMIDATE DERIVATIVE; THYMIDINE; THYMINE; UNCLASSIFIED DRUG; WATER;

EID: 23644447557     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200400422     Document Type: Article
Times cited : (53)

References (62)
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    • note
    • We obtained four to six structures for each regioisomer by systematic search of dihedral angles shown in Figure S1 (see Supporting Information), making changes of 30°. From these structures, we chose the one with the lowest energy that kept all the six key hydrogen bonds. This best intermediate was geometry-optimized with further systematic search of a dihedral angle of approximately 10-20°.
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    • note
    • The IUPAC name of this class of derivative is methyl(alkylamido) phosphonates.
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    • note
    • To identify hydrogen bonds, a donor-acceptor separation of less than 3.20 Å and a donor-hydrogen-acceptor angle of 120° or greater are required.
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    • note
    • Synthesis of the 5′-methoxyacetylamino derivative was also much faster (2 h) than that of the 5′-butyrylated derivative (32 h).
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.